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They Indicted His CFO. But Is Trump Really Next?

They Indicted His CFO. But Is Trump Really Next?
James Devaney/GC Images via Getty

Now that the grand jury has issued true bills indicting the Trump Organization and its longtime CFO, Allen Weisselberg, for a litany of financial-related crimes, legal experts and pundits have been busy analyzing the charges for clues about what's next. Opinions seem to fall into three buckets: pessimistic, cautious, and excitedly optimistic. Let's walk through them.

The Pessimistic View

Former lead counsel for the House Impeachment inquiry, Daniel Goldman, doesn't believe that Trump is likely to be charged. While his cynicism may be informed by his experience with an impeachment process that ultimately was buried by the Senate, Goldman had some interesting points that should be considered.

Goldman takes as a starting point the simple truth that when your goal is to flip a defendant such as Weisselberg, you usually throw everything you have at him. Goldman believes that's what happened here, and what we see in the indictments is about as strong a case as anyone could make. He thinks it's a strong case…against Weisselberg.

But here's where the case starts to look weak to him. Ordinarily, a corporate defendant like the Trump Organization is the last defendant you charge in such a case because you want to see which individual defendants will be flushed out by the investigation. To Goldberg, it would be unusual to charge the company later with more crimes, despite a continuing investigation. So Goldman doesn't believe more charges are coming against the Trump Organization itself, which will be a disappointment to many.

He also doesn't believe either that Weisselberg will flip, or that you can prove a tax, insurance, loan or accounting fraud case against Trump (who does not email or text) without the cooperation of Weisselberg. That cooperation is the thing that would pin Trump to the fraud, but so long as Trump maintains that it was all Weisselberg's doing and he just signed wherever Allen told him to sign, and that's all the evidence there is, Trump can't be convicted.

This may be the real reason, some argue, why Cy Vance decided not to run again for DA: He didn't want to be there when the bad news about no charges for Trump dropped.

The Cautious View

Former federal prosecutor Renato Mariotti exemplifies the more cautious approach. In a thread, he laid out why the case against Weisselberg is very solid because the case is actually quite simple: for at least 15 years, the Trump Organization paid Weisselberg in the form of apartments, cars and tuition and deducted those as expenses, but Weisselberg never paid taxes on that in-kind income, nor did the Trump Organization pay any payroll taxes on it. That is a scheme any jury can get its head around, Mariotti believes.

Moreover, it's clear the defendants knew what they were doing, the money amounts were significant (over $1.7mil of in-kind benefits with over $900K in taxes owed), and Weisselberg's fingerprints were all over it, including his signature on the lease for a free apartment. Unlike Goldman, however, Mariotti isn't ready to say that Weisselberg won't flip in the face of these charges, noting that the pressure to do so is higher than it was just the day before.

Some, like former Trump fixer Michael Cohen, have argued that it actually won't even be necessary for Weisselberg to flip in order for Trump to be charged. We don't know the extent of the documentary evidence, but Cohen insists from his own experience that Trump's name is all over it. Thus, even if it's true that Trump doesn't email or text as Goldman laments, there may be other ways to tie him to financial fraud within the company. "Everything went through Donald," Cohen told CNN. "Every single thing, whether it was the acquisition of paperclips, light bulbs, furniture, mattresses, you name it. Allen Weisselberg's kids' payments, rent, everything would have a Donald Trump signature on it or his initial."

There may be other witnesses willing to testify, too. For example, an "Unindicted Co-Conspirator 1" named several times in the indictment has since been identified as Jeff McConney, the longtime Controller for the Trump Organization. McConney has already appeared and testified before the grand jury about how the company operates and how it handles compensation. McConney received something called "transactional immunity"—meaning he can't be prosecuted for the things said to the grand jury. It is therefore quite possible that McConney is already cooperating with prosecutors and could provide eye-witness testimony that goes to Trump's knowledge of fraudulent activity, meaning again that Weisselberg's cooperation isn't needed to make the case.

The Optimistic View

Those wishing to find good news in the indictment have plenty to point to, including the fact that not only is there an Unindicted Co-Conspirator Controller who may be cooperating, but there are two other company employees and several Trump Executives who have yet to be named or charged. The two employees are most likely Trump's former bodyguard turned Chief Operating Officer, Matthew Calamari, and his son Matthew Calamari, Jr., who both received rent and cars free of taxes. They might be prime targets to flip even if Weisselberg refuses.

More tantalizing to the optimists is paragraph 15 of the charges, which specifies that "the defendants misreported portions of the employee compensation paid to certain Trump Organization Executives…in the form of checks drawn upon other Trump Organization Entities." For those familiar with the ongoing investigations of the entire Trump family, this was a shot across the bow of Trump Organization executive Ivanka Trump, who the New York Times earlier reported had received "consultant" fees totaling $747,622 as part of the $26 million in deduction that Trump used to reduce his taxable income over several years on numerous projects.

Ivanka Trump was a paid employee of the Trump Organization at the time but also controlled the LLC into which this money was paid. There are a host of potential issues with this kind of payment, including whether it was market-based and competitive, whether Ivanka actually did anything to earn that money, and importantly whether it was a way to compensate her while avoiding payroll taxes for the Trump Organization since her consulting company was issued a 1099 instead of her being issued a W2 for that income. However Weisselberg was receiving income off the books may also have been the way Ivanka and other executives (including her brothers Don Jr. and Eric) were paid. If demonstrated, that would be a very bad fact for the Trump children.

Optimists will also point to the statement by Attorney General Letitia James, who said yesterday that the indictment was an "important marker in the ongoing criminal investigation of the Trump Organization and its CFO, Allen Weisselberg….The investigation will continue, and we will follow the facts and the law wherever they may lead." A "marker," the optimists note, is just that—one milestone in a longer story, and they are eagerly anticipating more news to come.

So which of these views is the most sound? I personally lean into the cautious approach because we simply don't know enough to predict with any confidence what the next steps of the investigation will be. That is actually good news because it also means the defendants and other potential defendants don't really know anything either. This sets up a strong incentive for those who are willing to flip to do so early and get the best deal they can from prosecutors. I suspect that the charges against CFO Weisselberg are intended not only to add pressure for him to cooperate but also to demonstrate to everyone else that the gig is up around unreported incomes and that charges could be in the works for them, too.

We may enter a fairly quiet period because the trial of Weisselberg won't begin for quite some time. Indeed, the parties likely won't even be back before a judge until September due to a backlog in the courts from the pandemic. During this time, investigators will continue to turn over stones to discover what might be crawling around beneath them. None of that is good news for Donald Trump, whose only defense so far to the charges has been that they are unfairly being applied to his company and not to others. That "witch hunt" may have an emotional appeal to his base, but it isn't a legal defense at all.

One final thought: If it turns out that Trump knew exactly what he was doing by reducing his own taxable income without his company having to pay any payroll taxes on millions in otherwise taxable employee benefits, he's as deep in this fraudulent conspiracy as Weisselberg is now. That means that it's not just his alleged misrepresentations of Trump property values to banks and to tax authorities that could bring him down. It's also just plain ol' tax evasion—the well-understood Achilles heel of other notable crime families.

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